Synthesis, crystal structure, anti-cancer, anti-inflammatory anti-oxidant and quantum chemical studies of 4-(pyrrolidine-2,5-dione-1-yl)phenol

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F21%3A00549370" target="_blank" >RIV/61388955:_____/21:00549370 - isvavai.cz</a>

Výsledek na webu

<a href="http://hdl.handle.net/11104/0325382" target="_blank" >http://hdl.handle.net/11104/0325382</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2020.129267" target="_blank" >10.1016/j.molstruc.2020.129267</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis, crystal structure, anti-cancer, anti-inflammatory anti-oxidant and quantum chemical studies of 4-(pyrrolidine-2,5-dione-1-yl)phenol

Popis výsledku v původním jazyce

4-(Pyrrolidine-2,5-dione-1-yl)phenol (PDP) prepared by establishing a new protocol from 4-aminophenol and succinic anhydride using glacial acetic acid as a solvent. The structure of PDP was initially verified by FT-IR, H-1 and C-13 NMR spectroscopy and further confirmed by single crystal XRD and mass spectrometry techniques. These properties of PDP were also evaluated by DFT, TD-DFT and quantum chemical methods. The molecular structure of PDP was computationally examined by density functional theory (DFT/B3LYP/cc-pVTZ and DFT/PBE0/cc-pVTZ methods). The MEP map shows that phenyl ring with negative electrostatic potential while pyrrolidine ring has slight positive electrostatic potential. Vibrational assignments, chemical shifts and geometrical parameters (bond lengths, bond angles, torsion angles) of PDP were calculated and found in good agreement with experimental results. The computed mass spectrum also exhibited important peaks including the base peak. PDP has higher anti-inflammatory activity 64.9 +/- 2.2% at 50 mg/kg as compared to standard COX-1 inhibitor Ibuprofen 47 +/- 1.9%. The anticancer activity also exhibited significant inhibition of cancer for HT-29 cell line. The results imply the possible anti-inflammatory application of the compound beside some structural modifications may lead to establishing a new anticancer drug. (c) 2020 Elsevier B.V. All rights reserved.

Název v anglickém jazyce

Synthesis, crystal structure, anti-cancer, anti-inflammatory anti-oxidant and quantum chemical studies of 4-(pyrrolidine-2,5-dione-1-yl)phenol

Popis výsledku anglicky

4-(Pyrrolidine-2,5-dione-1-yl)phenol (PDP) prepared by establishing a new protocol from 4-aminophenol and succinic anhydride using glacial acetic acid as a solvent. The structure of PDP was initially verified by FT-IR, H-1 and C-13 NMR spectroscopy and further confirmed by single crystal XRD and mass spectrometry techniques. These properties of PDP were also evaluated by DFT, TD-DFT and quantum chemical methods. The molecular structure of PDP was computationally examined by density functional theory (DFT/B3LYP/cc-pVTZ and DFT/PBE0/cc-pVTZ methods). The MEP map shows that phenyl ring with negative electrostatic potential while pyrrolidine ring has slight positive electrostatic potential. Vibrational assignments, chemical shifts and geometrical parameters (bond lengths, bond angles, torsion angles) of PDP were calculated and found in good agreement with experimental results. The computed mass spectrum also exhibited important peaks including the base peak. PDP has higher anti-inflammatory activity 64.9 +/- 2.2% at 50 mg/kg as compared to standard COX-1 inhibitor Ibuprofen 47 +/- 1.9%. The anticancer activity also exhibited significant inhibition of cancer for HT-29 cell line. The results imply the possible anti-inflammatory application of the compound beside some structural modifications may lead to establishing a new anticancer drug. (c) 2020 Elsevier B.V. All rights reserved.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

1872-8014

Svazek periodika

1224

Číslo periodika v rámci svazku

JAN 2021

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

12

Strana od-do

129267

Kód UT WoS článku

000598932200006

EID výsledku v databázi Scopus

2-s2.0-85091195374